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Hydrogen Peroxide → 2-(6-Bromopyridin-2-yl)-2-methylpropanamide

HRID 385912
Notes
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Reaction equation

HRID 385912 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1.OO.C(=O)([O-])[O-:16].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:16])[CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 579696582-(6-Bromopyridin-2-yl)-2-methylpropanenitrile

Product 1

HCID 595255632-(6-Bromopyridin-2-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (Example 367, Step 1) (200 mg, 0.89 mmol) in dimethylsulfoxide (4 mL) was added hydrogen peroxide (0.42 mL, 4.8 mmol) and potassium carbonate (1.23 g, 8.89 mmol). The reaction was then stirred overnight at 70° C. The resulting slurry was cooled to ambient temperature, filtered and directly purified by reverse phase HPLC (10-100% acteonitrile/water+0.05% TFA modifier) to yield the title compound.

Workup

  1. temperatureThe resulting slurry was cooled to ambient temperature
  2. filtrationfiltered
  3. customdirectly purified by reverse phase HPLC (10-100% acteonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-78b45d5989f648298460c2852aeefe9f
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367706B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes